Date: Thu, 25 Aug 2022 07:33:57 -0400 From: James Karvonen Subject: Song of the Lonesome Rails - 17. 17. The week passed slowly for Bobby. At nights he would go out on thedeliveries with Antonio sometimes returning as late as 8:00 in the morning. During the day he would sleep resting his aching muscles. Working with Antonio just about each and every night was no easy chore. During those nights when he worked with Antonio he saw very little of Kim during the day because during the day he slept. At least he was earning some money. He already had close to thirty dollars saved thanks to his job working with Antonio. Already he had planned to send half of that money to his mother. The only thing he needed in order to do that was an envelope and stamp. The money that Antonio gave him after he finished his night deliveries he kept in an old sock that he had hidden underneath his pillow not that anyone would steal from him at the boarding house, besides business was really slow. Mr. Johnson the man who Bobby first met had left. Mr. Johnson had been the only boarder for several weeks. A couple of traveling salesmen appeared, but due to the business they were in they only stayed for a couple of days then left. Right now there were no boarders at the boarding house, so business was really down. A couple of days before Labor day, Bobby decided to do something that he had been meaning too for quite some time. He went into town and with some of the money he had earned purchased a couple of stamps, envelopes a click pen and paper. He was going to write a letter to his mother who was probably worried sick about his health and welfare.He felt sure that she had already been notified about his escape from Pine Island. He also felt certain that the police had been over to the house several times looking for him. He sat down at the desk in the attic bedroom, then tore out a piece of paper to write the letter on. He had a couple of hours to go before he would leave with Antonio to make their next deliveries. Kim hadn't returned yet from selling her newspapers at the train station to the commuters returning from Washington D.C. so he pretty much had some time to himself. He wanted to write the letter as soon as possible so that he could put the letter in the mailbox to be sent out before he went on his delivery run with Antonio in a couple of hours. He was nervous about this letter because he wasn't sure how his mother would respond. At least she would know that he was safe and she would have some money to spend on his family. He looked down at the blank sheet of paper lying on top of the desk. With trembling hands and tears in his eyes, he started to write.. Dear mom, I am sorry that I hadn't written to you sooner. As you know I am on the run. I couldn't stay at Pine Island any longer because that place is really bad. I am staying with some people at a town called Pointe of the Rocks, Maryland. I'm not sure how much longer I will be Staying here. What I want to do is go to California and get with dad and try to get him to send for you, so it may take a while. I am having to ride the rails to get to California, and I don't mean on a passenger train. So I may be leaving this place soon. I will also be working at different places while I take this cross country trip. I have already earned thirty dollars. I am sending you half of the money that I have already earned for you and Randy. I know that you will need this money to make ends meet. Whenever I can l will be sending you more money. That's all I have to say for now. I will write you again soon and let you know where I am and what I am doing. Please don't worry about me because I will be okay... ??? All my Love, ??? Bobby . Bobby addressed the envelope then went on ahead and put the letter that he had just wrote into the envelope. He added fifteen dollars, then sealed the envelope, putting a stamp on it. Well that's that, he thought. He felt much better now that he had written the letter. That night when he went out with Antonio to make his night time deliveries, the very first thing Bobby did was to put the letter into the mail box. Labor day was only a day away. After Labor day Kim would probably start going back to school. That would give Bobby even less time to be with Kim. Bobby's could not help but to ask himself, how much longer mind now was how much longer he would be staying here with Kim and his mother. With Kim about ready to start back to school there could be a problem with truant officers. After all at twelve he was still very much a minor. If a truant officer were to come around and see that he wasn't in school that definately could pose a problem for him. There was always that possibility of being questioned by the truant officer. And if the truth were to come out that could be a one way ticket back to Middletown New York and ending up back to Pine Island and given added time for escape. Yes there was a lot of things that he had to worry about and sooner or later he was going to have to make a decision one way or the other. And he would need to make that decision soon. Labor day finally did arrive. It was a joyous holiday that the whole town of Pointe of Rocks celebrated. Because it was a holiday it was also a night that Antonio decided to take off. Besides most of the places that he would be making his deliveries too would probably be closed because of the holiday. He still had a several more deliveries to make and then he would have t go back to Canada to pick up another load to so that he could replenish his stock. They had just finished their meal of Roast beef and all the trimmings. After Dot and Kim had cleared the table and put up the leftover food, Antonio stood up to make an announcement."Being that tonight is a holiday I propose that I open up one of my bottles of Canadian brewed whiskey and we all celebrate and have a drink." "I like that idea, what about you two? Would like to have a drink with us to celebrate the holiday?" Dot asked "Sure mom. I would enjoy a drink." Kim piped. "What about you Roberto. You work hard with me every night, why don't you have a drink with us?" Antonio smiled. "I never tasted whiskey before, but since Kim is going to have a drink then I might as well have a drink also." Bobby decided. "Very good. I will go get that extra bottle of whiskey from my truck. I'll be right back." Antonio replied, leaving the table. While Antonio had gone to get the whiskey, Dot went into the other room to get four wine glasses. When she returned she set the glasses down on the table. "Here we go love." Antonio said returning with an unopened bottle of whiskey. Opening the bottle of whiskey Antonio poured them all drink. Sitting down at his place at the table, he lifted his wine glass and said, "A toast to a prosperous year." For the first time Bobby tasted whiskey. It burnt his mouth and throat causing him to cough a little. He was about to spit it up but somehow he managed to keep himself from doing that. It definitely would have been an embarrassment if that were to have happened. Looking over at Kim, Kim did not seem to be bothered by the whiskey at all. She went on ahead and took another sip. He would just have to take smaller sips, he concluded. But with everyone drinking around him including Kim, he forced himself to drink a little more of the whiskey. He didn't know if he would ever develop a taste for whiskey because quite frankly he didn't like it. It took a while but he finally finished drinking his glass of whiskey. He was beginning to feel a little woozy and lightheaded. Antonio poured himself another glass of whiskey then poured some for Dot. Looking over.at Bobby and Kim he asked,"Would you two like some more?" "No thank you." Bobby said. Kim politely shook her head. "One drink is enough for me." she said. "Come on Roberto join me in one more drink. this stuff will grow hair on your balls." Antonio chuckled. "No, I really don't want anymore." Bobby replied. "Oh well." Antonio said, putting the bottle down. He and Dot went on ahead and fiinished their drinks. "And now since we are all well fed and had a few drinks, I propose that we all go into the master bedroom to relax and enjoy each others companionship for the night. After all tonight is holiday, and we should make the best of it. We can sleep as late as we want too tomorrow morning.." Kim looked over at Bobby and nodded. She, grasped his hand knowing that he might be a little apprehensive about all this."Come on Bobby. This is going to be a big night for you. I'm sure you're going to enjoy it. And who knows you might actually learn something." Bobby was apprehensive about this but he knew that it would upset Kim if he didn't go along with what Antonio and Dot wanted to do. He took a deep breath then nodded. "Alright, I guess." He said. Kim gave Bobby a hug and a quick kiss. Bobby could used that Kim was very excited about this. They stood up and headed upstairs to the second floor to the master bedroom where Dot and Antonio slept when he came over. The bedroom was large with plenty of antique furniture and a large walk in closet. Everything in the bedroom was draped in pink including the carpetted floor. Like Kim's bed, Dot slept in a king size canopied bed. The whole room smelled of incense. "So now that we are all together, why don't all of us get a little more comfortable." Antonio suggested. "Yes, why don't we." Dot smiled. She walked over to Bobby, then placed her hand on his shoulder. "You're not going to be shy, are you dear. I understand that this will be a whole new experience for you. Kim told me all about you. She even told me that she took your virginity. So I'm sure you have an understanding of what will be going on when we occasionally get together like this. You've been very helpful to me since your arrival here. And so you should be part of this, and dear Antonio thinks the world of you, don't you Antonio? "Roberto you are a hard worker. If I someday would have a son, I would hope that my son would be like you." Antonio complementary said. "And I've enjoyed being with you the times that we had been together." Kim added. Bobby didn't know what to make of all this. They were all complimenting him, but complimenting him for what? "So, are you all ready to get a little more comfortable?" Antonio asked. "I'm ready." Kim said, and she was the first to start undressing. Her mother started undressing also. Antonio walked over to Bobby. Putting his arm around Bobby's shoulder Antonio drew him close saying, "Roberto, I want you to understand that anything we do with you or with each other that you feel uncomfortable with, please do not hesitate to let us know. We don't want to force you into doing something that you do not want to do. Some of the things that we do with each other you might not understand. But the main thing is that we want you to be comfortable with us and your own body. So if you want too, you could undress and join us, or if you prefer you can just sit back and watch and see what we do together. But either way we would like for you to be part of this. That will be your choice Roberto." Bobby knew that Kim would be upset if he didn't join them in whatever they were going to do together. That was the last thing Bobby wanted, and that was for Kim to get upset with him. Kim had opened up a whole new world for him, and he didn't want to see that world destroyed. He glanced over at Kim and her mother who were both naked and standing next to each other. He could not help but to notice Dot's large breasts, the curves of her hips and the thick vee of reddish brown pubic hair that covered her vagina compared to Kim's nude body who's breasts were much smaller and who's vagina could clearly be seen beneath the scant wisps of her pubic hair. Looking at them standing side by side next to each other caused a stirring in his loins which told him that it wouldn't be long before he would become erect. Taking a deep breath, Bobby started unbuttoning his shirt. When he had it all the way unbuttoned he pulled his shirt off baring himself to the waist. "You are a good boy Roberto. I see that all that hard lifting you have been doing with me when we unload and carry those crates on our deliveries is building up your muscles. Here Roberto, show us those muscles in those arms of yours that you are working on." Antonio grinned. Sucking in his belly, Bobby flexed both of his arms posing for them like a boxer who had just won his fight. "Ah what did I just tell you, your biceps are getting bigger every night we work together or they not?" Antonio grinned, clenching his hand gently around Bobby's left bicep. " See that, I can barely get my fingers around your bicep." He smiled. Releasing his grip around Bobby's left arm, Antonio gently slapped Bobby's taunt stomach just over his belly button. " And look at that stomach of yours. All muscle, no fat, do you see that? When he works hard, his body becomes strong." Kim and her mother walked over to join them. As close in proximity as they were to Bobby, the inevitable had happened. Beneath his pants his penis had become erect. "The longer you work with Antonio, the stronger you will become as you grow." Dot pointed out. "Yes, he will become very strong indeed. But where else are you strong Roberto, down there perhaps?." Antonio asked with a twinkle in his eye. He pointed down at Bobby's crotch. The way Antonio was talking Bobby knew what he wanted him to do. Leaning over, he untied his both of his shoes then took them off. Taking a deep breath Bobby moved both of his hands down to the front of his pants then started unbuttoning his fly to open up the front of his pants into a vee. With some hesitation he slowly started pulling his his pants down. Freed from the confinement of his pants Bobby's slender erection snapped into view. He pulled his pants the rest of the way down over his stepping out of them. He stood there in front of them his face flushed red with embarrassment just as naked as Kim and her mother were . "Yes Roberto, I see that you are strong down there." Antonio smiled, reaching down to grasp Bobby's erection at the root. Gently he started flipping the slender shaft up and down while Kim and her mother watched. "And when you become a man your penis will be even longer and thicker then it is now and that will make you even stronger." Dot added watching with interest. Releasing his grip from around the root of his penis Antonio moved his hand down to Bobby's medium size scrotum. He cupped the soft wrinkled sack in the palm of his hand, lifting it up. Gently he started bouncing the twin orbs contained loosely in the sack up and down. "And here you will someday produce the seed that will make many babies." Antonio grinned. He moved his hand out of the way letting Bobby's scrotum drop back down in place between his legs. "And now, you must get undressed also Antonio." Dot said. "Yes Uncle Antonio, you must get naked with us." Kim piped. "Oh, but of course." Antonio smiled. He started undressing. Within seconds he was naked. Now it was Bobby's turn to stare. Antonio's lean well built olive toned body was all muscle and no fat. His chest looked as if it was carved out of stone with just a sprinkling of black hair growing. His biceps and triceps well formed and muscular. He had a washboard stomach centered by an outie belly button and love line of black hair stretching from his belly button down to his thick vee of curly black pubic hair that fanned outwards at the root of his rigid penis. His erection was thick and veiny angling upwards at least seven inches in length if not longer. He was uncircumcised, the foreskin drawn back to reveal a bulbous deeply blushed moist purplish red glans. His large plump hairy scrotum hung low between his muscular thighs. "Antonio is well hung, isn't he." Kim pointed out looking over at Bobby. "I guess you, you can say that." Bobby stammered. Compared to Antonio, Bobby felt inferior, but he had to consider that after all Antonio was a man in his mid thirties and he was just a twelve year old boy going through the the changes that someday would turn him into a man. He hoped that when he grew up he would be as strong and as muscular as Antonio was now. "So Kim, let me look at you. It's been a while since we had last gotten together like this hasn't it?" Tenderly put placed her hands on Kim's shoulders turning her around so that they were facing each other. "Yes mom, it has been a while." Kim replied. "Your breasts look like they have gotten larger." She said, moving both of her hands down to cup and fondle her daughters breasts. She ran her thumbs over Kim's springy nipples. "I think they have gotten a little larger also." Kim smiled. She gave Kim's breasts a little squeeze then dropped down on her knees in front of her. "You're starting to grow hair now, that's good. Last time we were together like this you didn't have no hair yet." She ran the palm of her left hand over Kim's vagina, causing the plump lips to open up a little revealing Kim's moist cleft. "I had been wondering when I would start growing hair down there. Now I'm glad that that is happening." Kim smiled. "Let's see how your love bud is doing." Dot said. She pushed the tip of her middle finger into Kim's moist cleft causing Kim to flinch. When she started wiggling her impaled finger inside of her, Kim let out a little cry. "Yes, it's just like it should be. Sweetie you are definitely turning into a woman." Dot grinned, sliding her finger out. Watching mother and daughter relating to each other the way they were doing now caused Bobby's penis to throb. Even though no contact was being made Bobby's rigid penis was throbbing to the point that even the slightest contact could cause him to climax. From behind him Antonio walked over to Bobby sliding his arm around Bobby's shoulders. Bobby jumped a little then settled down when he realized what Antonio was doing. "Watching what mama and daughter are doing together is making you horny, isn't it Roberto?" Antonio asked. "I guess." Bobby replied. "It makes me horny also." Antonio admitted."But each time we get together like this, she always examines her daughter like that." Dot stood up, then gave Kim a kiss on her cheek. She then said, "Honey, why don't you entertain Uncle Antonio for a little while. I would like to get to know your friend a little better." "Okay mom." Kim said. "Well Antonio, it looks like I have to go. I know that Dot will take good care of you." Roberto said. He walked over to Kim who was waiting for him. Kim took hold Antonio's hand then led him over to the large king size bed. Dot slowly approached Bobby swinging her hips seductively. Facing Bobby she placed one hand on his shoulders then brushed away his unruly cowlick with her other hand. Looking down at him, she asked, "Bobby, are you feeling a little more comfortable now?" "I guess." Bobby murmered. His rigid penis throbbed with each of one of his rapid heartbeats. The warm rising itch within his loins seemed to be really intensifying now because Dot was so close to him. She smelled really good having put some type of perfume on, but the perfume that she was wearing was beginning to make him woozy, almost light headed. "You look a little tense right now. But dear Bobby, you don't need to be that way, I want you to feel nice and comfortable with me." Dot cooed Looking over Dot's shoulder at the king size bed Bobby could see that Kim and Antonio were in an intimate embrace, their bodies pressing tightly together. They were hugging and kissing each other and rolling around on the bed with Kim ending up lying on her back looking up into Antonio's dark seductive eyes. "I see that you are into what my daughter and Antonio are doing together. That's the same thing we could be doing together if that's what you want sweetie. Even though I am Kim's mother, you do think I'm still pretty now, don't you?" "Oh yes." Bobby croaked. In his eyes Dot still was attractive. Breathing hard and deep his rigid penis throbbed even more because he was getting really close to his breaking point. Beads of sweat were forming on his forehead and chest. "I'm glad you find me attractive. Now if we could go over to the bed, I would be more then happy to take care of this for you." She said reaching down to tenderly fondle Bobby's penis. She grasped it with her thumb and forefinger beneath the now slippery head. That touch was all it took to bring Bobby over the edge. Letting out a cry, Bobby's rigid penis jerked hard in response to Dot's touch then started spasmatically started jack hammering away. A couple of squirts of clearish semen spat out out between Dot's fingertips as she held him hitting her upper thigh. A little more dripped onto Dot's still clenched fingertips. "Of my, you couldn't hold it, could you sweetie. But that's okay. I know that boys as hot as you are right now can have multiple orgasms so let's just say that that was only the beginning?" She smiled. letting go of Bobby's slowly wilting penis. When he was flaccid, Dot wrapped her arms around Bobby's smooth body pulling him up against her body to give him a hug. Feebly Bobby returned her hug. As they were hugging each other she tenderly kissed on his sweet moist lips. Relinguishing her embrace she gently took hold of Bobby's hand and led him over to the bed where Antonio and Kim were still going at it with each other. Bobby found himself unconsciously staring at them. Kim was lying on her back, her legs open in a V. Antonio was kneeling between Kim's outstreched legs, both of his thumbs parting Kim's swollen vaginal lips. His mouth was just above the gaping moist pink cleft his tongue darting in and out of her. Every now and then he would pause to flutter his tongue instead of darting it in and out. In response to Antonio's active tongue, Kim was arching her back and rolling her head back and forth on the soft fluffy pillow. Several times she cried out in sheer escasy. "As you can see Bobby, Antonio and my daughter Kim are enjoying each others company. But don't concern yourself with what they are doing together right now, Instead, focus in on what you and I will be doing together in a few minutes, can you do that sweetie?" "Yes." Bobby whispered. Dot leaned over Bobby and kissed him on his forehead then said, "Now, I want you to lie on your back next to Kim. There is plenty of room on the bed for you to do that. Antonio paused momentarily from performing oral sex on Kim. He lifted his mouth off of Kim's hot wet vagina then looked over at Dot saying, "I see you've decided to join us." "I'm not going to let you have all the fun now, am I?" She laughed. Panting Kim braced herself up on her elbows looking over at Bobby and her mother. Her mother was standing at the side of the bed waiting for Bobby to lie down on the king size mattress next to her. Bobby eventually did lie down on his back ontop of the bed about three feet away from her. Dot sat down on the bed on the other side of him." "Can we watch and see what mom is going to do with Bobby ?" Kim asked her faced still blushed from what Antonio had done to her before. She was curious about what her mother was going to do with Bobby. Besides, not only would it be exciting for her to watch, but it would be fun also. "Of course we can. I would be interested in watching also." Antonio. smiled. He made himself comfortable sitting down on the bed besides Kim. Dot was gentle. She reached down to tenderly grasp Bobby's soft penis. It was sticky around the spongy head from Bobby's recent ejaculation only a few minutes ago. "First of all, we need to wake this little guy up first. After what just happened a few minutes earlier it's taking a little nap." Dot chuckled. As Bobby laid there, Dot started rubbing his soft shaft beneath the helmet head up and down pausing every now and then to give the shaft a little squeeze. He felt a slight pleasant tingle in his loins, but knew that it might take him a little while for him to get hard again. He just laid there and trying to relax as Kim's mother did her thing. Dot stroked his penis up and down for another minute or so then surprised Bobby by leaning over him so that she could take the entire two and a half inch length of his soft slender shaft into her mouth, her lips pressing against his smooth pubic mound. He gasped when he felt the warm wetness of Dot's mouth around him and her hot wet tongue swirling and darting against the most sensitive areas of his penis. She lifted off his penis a bead of spittle snapping wetly between them. She then started stroking him up and down for about a minute or so, then took him into her hot wet mouth again. It didn't take long for Bobby's slender penis to start lengthening. It didn't take long for Bobby to become erect again, his four slender inches proudly standing straight up from his hairless mound. "There we go sweetie. Now you're nice and hard again." Dot said, holding Bobby's erection with her thumb and forefinger upright at the root. She waggled his rigid length back and forth a couple of times. "What are you going to do?" Bobby asked. Already his penis was throbbing pleasantly again "You,ll see, let me know when you're about ready to cum again." Dot said. She started off by stroking his rigid shaft up and down several strokes, then stopped, only to lower her mouth down around him so that she could suck him off. That was something that Bobby hadn't felt since Andrew, one of the guards at Pine Island had sucked him while he was in the hole bringing him to an intense gut wrenching climax. And now it was happening again. Dot would lift off then stroke him for another several strokes only to stop so that she could suck him off again. Finally Bobby had reached his point of no return. His whole body tensed his heartbeat rapidly beating, his breathing having become deep and rapid. "I'm going to do it!" He finally gasped. And then Dot did something was totally unexpected. Instead of bringing him the rest of the way off, just as he was about to climax Dot grasped Bobby's throbbing length with her thumb and forefinger just beneath the head and squeezed the shaft tightly as hard as she could stopping him from ejaculating his semen. His shaft swelled outwards and throbbed a couple of times beneath Dot's tightly clenched fingertips. Finally the urge to ejaculate receded, but Bobby still maintained his erection. After a few seconds she loosened her grip then started stroking his slender rigid length up and down again. When Bobby was at the verge of cumming a second time she did the same thing, driving Bobby simply bonkers. "What are you doing?" He gasped. He was at the point now that he didn't whether he was coming or going. What she was doing to him simply put could be considered sexual torture. "I'm just trying to extend your pleasure. It won't be long now." Dot smiled. And then she continued doing what she had been doing to him. A few seconds later Dot gave Bobby the relief he had been begging for ever since Dot had started. Instead of using the squeeze technique on him a third time, she kept stroking until finally tremors shot through Bobby's now sweaty body. He climaxed like he had never climaxed before. Shudders ripped through his tense twelve year old body. His beet red shaft tightened within Dots stroking grip then bolted hard between Dots stroking fingertips to the point that it was actually straining. A second later Bobby's ultra stimulated erection started pulsing away at a rapid pace. Three ropes of thinnish boy cum spurted high into the air only to splatter back down on his heaving chest and stomach. More spilled down over Dot's still stroking fingertips. And then it was over. This was Bobby's most intense orgasm yet and it left him him virtually exhausted. Adding even more to his exhaustion Dot slid her cum dripping fingers all the way down Bobby's slowly wilting shaft then opening up her mouth went down on him taking his entire flaccid length into her mouth. Pursing her lips tightly around Bobby's shaft she stared sucking and bobbing swallowing his semen in the process. She didn't lift off until she had Bobby's now flaccid penis spit clean. "What a delightful little morsel that was dear boy." Dot said. She leaned over and gave Bobby a sensuous kiss on his lips. She kissed him again even deeper before finally lift in off. She looked across the bed over at he daughter Kim and Antonio. "That was a fantastic little show my love. I enjoyed watching it." Antonio exclaimed. He clapped his hands. "You really did it that time. Your jism shot high into the air and quite a bit more came out then what I've seen before." Kim observed. Bobby was virtually too exhausted to respond. For several minutes Bobby just laid there in his warm post orgasmic afterglow his body now totally relaxed. All he wanted to do right now was to fall asleep. "I think your little boy friend is worn out Kim." Antonio commented. "Yes, I think so also." Dot smiled, tenderly stroking Bobby's soft downy cheek. Then she looked over at her daughter she said, "Why don't you help Bobby to his room. I believe he's had enough fun for tonight." "Okay mom." Kim replied. "Come on Bobby, I'll take you to your room." Slowly Bobby eased off the bed. He picked up his clothes then still naked followed Kim out of the master bedroom. It didn't take long for Bobby to get to his upstairs room. "Did you have fun tonight?" Kim asked. "Your mom really knows about sex, don't she? She brought me off like I had never been brought off before." Bobby admitted. "I told you, she use to be a masseur. And masseurs do other thingds then just give their clients massages. Anyway I have to get up early tomorrow so I'm going to leave you alone to get some sleep. It looks you need it, besides you have to work with Uncle Antonio tomorrow night, don't you." "Yeah, Antonio says we're going to have to leave a little earlier tomorrow night because we are going to drive to Baltimore." "Baltimore, I've only been to that city once. It is quite a ways from here." "I'll see you then sometimes tomorrow, won't I?" Bobby asked hopefully. He really enjoyed being with Kim. "Yeah, we'll get together sometime tomorrow afternoon. There is something that I want to do with you." "What's that?" Bobby asked. "I've always wanted a sister, so tomorrow I want to dress you up like a girl. I want to see what you look like wearing my clothes and makeup." "What!" Bobby gawked. "Come on Bobby, it'll be fun. You can always wash the makeup off afterwards before you go with Uncle Antonio." Bobby smiled inwardly to himself. At times he wondered what it would be like being a girl. So tomorrow he would find out. "Okay I guess, if that's what you want to do." Bobby relented.j With that having been said, Kim eased over and gave Bobby a kiss. "See you tomorrow," she said before leaving the room. iAfter the sex orgy that Bobby had with Antonio, Kim and Dot in the master bedroom that evening Bobby was virtually exhausted. As soon as his head hit the pillow that night he fell right off into a deep well deserved sleep. He never realized that sex could be so fun, yet exhausting. And he was exhausted. He couldn't remember how many times he had gotten off that night. It wasn't until a little after 9:00 the next morning that Bobby finally woke no. Not only had he been exhausted but when he woke up he was hungry. He dressed, took care of his personal hygiene then walked downstairs to the dining room. Dot was in the kitchen washing dishes. "Morning." Bobby murmered sleepily. "Well there he is, my little sunshine boy. Did you have a good nights sleep last night?" Dot asked him cheerfully. "Yes ma'am." Bobby replied. "If your hungry, there are some Cheerios in the cupboard. Go ahead and help yourself." Dot exclaimed. "Thank you." Bobby murmered. He opened up the cupboard and took out the box of Cheerios. Walking over to the refrigerator he opened it up and took out a bottle of milk. Dot gave him a bowl and to pour the Cheerios and milk in. Sitting down at the table Bobby added some sugar to he s Cheerios then started to eat. "Did you have a good time last night?" Dot asked. "Yes ma'am." Bobby answered truthfully. "Every now and then we get together like that. Its not like we do it all the time." Dot explained. Bobby nodded between mouthfuls. He could feel himself once again getting hard just thinking about everything that had gone down last night. Sitting at the dining room table he fidgetted uncomfortably. "Antonio says he's going to be here around 4:00 and wants you to be ready to go at that time." "Where is Antonio now?" Bobby asked. "Taking care of some business." Dot answered. Knowing that Antonio was a gangster Bobby could only imagine what type of business Antonio would be taking care of. "Kim should be back in a couple of hours or so. After delivering her papers at the train station this morning she told me that she had to do some other things, so she'll be back here around 1:00 or so. You still have a little yard work to take care of don't you?" "Yes ma'am, I still need to do a little weeding around the flower garden" "So that should keep you busy until Kim gets back." "Yes ma'am." Bobby said. He liked to keep himself busy. Not only did it give him something to do, but keeping busy took his mind off of things that bothered him. He finished up eating, then taking his dishes to the kitchen sink set them into it. Standing up he left the dining room then headed outside to finish weeding the flower garden. Already this early in the morning it was getting hot outside. He took off his shirt to get some sun, then proceeded to weed the garden. He could not help but to think about what Kim told him last night. She wanted to dress him up as a girl. That would be a first, Bobby thought, though he always wondered what it would be like being a girl. About an hour later Kim appeared walking down the sidewalk to the boarding house. Bobby stopped what he was doing and watched. He was all hot and sweaty now and smelled a little ripe. Walking over to him Kim stopped, then said "I see mom has you working this morning." "Not really, I just wanted to get this done." "Did you have fun last night?" Kim asked. "Uh huh, it was different, that's for sure." Bobby replied. "What happened last night don't happen all the time. Its only when mom and Antonio get to drinking some, anyway I still want to dress you up as a girl sometimes this afternoon." Kim stated. Bobby smiled inwardly to himself. Kim was unlike any girl Bobby had ever met, not that he was into girls all that much. "Antonio is going to take me with him at 4:00 this afternoon, so I'm going to have to get ready for that." Bobby stated. "You have plenty of time before Antonio picks you up, its not even twelve yet." Kim emphasized.i She really wanted to do that with him, Bobby thought. Oh well, might as well get it over with, Bobby decided. "Let's go ahead and do it now, I'm going to go ahead and get a shower first. As you can see, working out here all morning has made me nice and sweaty." He lifted his left arm to take a wiff of his hairless armpit. "I even got a little B.O." "You don't have to take a shower first, I like you just the way you are, besides you'll probably want to take a shower afterwards to get all the makeup I'm going to put on you off." "You're going to put makeup on me?" Bobby exclaimed. "Ah huh." Kim new nodded. "Come on, I'm dying to see what you would look like as a girl." Bobby hadn't been expecting that. He just shrugged then followed Kim into the boarding house. Once inside they headed up the stairway to Kim's room. Opening the bedroom door, Kim motioned for Bobby to go in first. Bobby walked into the room while Kim followed. She closed the bedroom door behind her. Sitting down on Kim's bed, Bobby watched as she opened up the top drawer of her dresser and took out a washcloth. "What are you going to do with that?" Bobby asked inquisitively. Carrying the washcloth over to where Bobby was sitting at the edge of Kim's bed, she said. "Stand up." Bobby did as Kim instructed him to do. Standing up Kim faced him then said, "You're pretty sweaty so I'm going to wipe you off a little." Bobby just shrugged, allowing Kim to do what she wanted to do. Reaching over towards Bobby, Kim used the washcloth to wipe off Bobby's sweat glistening chest. "It would be nice if I had an electric fan in this room." "It is kinda warm in this room, isn't it." Bobby said. "Wait until later on this afternoon when the sun shines into my bedroom window." Kim said. She took her time wiping the sweat off of Bobby's firm chest and taunt stomach. She worked the washcloth down to the waist band of Bobby's pants. "There, now turn around." Bobby did so standing there as Kim wiped off his shoulders and upper back. She slid the washcloth down Bobby's spine so that she could wipe the sweat off of his lower back. When she finished she said, "There! Now I can get to work on you." She beamed. Even though Bobby was no longer sweaty, he still felt hot in more ways then one. His penis was stirring beneath the tight confinement of his pants. Kim was definately arousing him, giving him the attention that she was giving him right now. Slowly he became erect, which in a way was embarrassing to him, becoming rigid like that at the wrong time and place. He hoped that Kim wouldn't notice the tenting at the front of his pants. Setting the washcloth off to the side Kim walked back over to her dresser. Opening the top drawer she took out one of her training bras along with a pair of white cotton bloomers. "What are you going to do with those things?" Bobby asked. "What do you think." Kim smiled setting her bra and bloomers down on her bed. "You're not going to make me put those on, are you?" Bobby protested. "I told you I wanted to dress you up as a girl, and that means everything. But before I have you put those on, I want to comb out your hair." Kim replied. "Gee Willigers Kim!" Bobby frowned. But deep down inside he found himself amused by what Kim wanted to do to him. He watched as she walked over to her bureau. Opening up the top shelf she took out a comb. "You're serious about all this, aren't you?" "Of course." Kim answered. She walked behind him then started to comb out his tangled hair. By the time she finished combing Bobby's hair his hair was almost shoulder length. "There, that looks better. Now you really are beginning to look like a girl." Bobby shook his head in disbelief. Kim really was serious about all this, he concluded. Now what? He wondered. Setting the comb down, Kim picked up Kim the training bra. "I'm going to put this on you now." "But I don't have no tits. Not like you at least." Bobby pointed out. "Quit complaining." Kim said. She slipped the training bra around him, tightening the straps at his back. She then walked back over to her dresser and took out a pair of knee socks. Wadding the knee socks up, she walked back over to Bobby and stuffed one of the socks in the left cup of her training bra, then did the same with the right cup. Once again she tightened the straps up. Stepping back a little Kim admired her handy work. "Now it looks like you do have tits." She laughed. "Don't you think your taking this a little too far Kim?" Bobby chuckled. "Of course not. I don't know about you but I'm having fun." "I'm sure you are." Bobby chuckled. "Now take your pants off." "What!" Bobby exclaimed. "You heard me. You're going to put these bloomers on." Kim stated. "There is no way that you would look like a girl if you wear those pants that you have on." Kim pointed out. Bobby shook his head. This was becoming an embarrassment more then anything else. He sucked in his stomach then unfastend the front of his pants then pulled them down. Since he was wearing no undrawers his now erect penis waggled proudly into view. Since Kim had seen him with an erection before this was no longer any big deal. "Hmmm." Kim said, looking directly at his slender erection. "Being hard like that would never due." Without saying another word Kim walked even closer to him, then dropped down on her knees in front of him. "What are you going to do?" Bobby asked. "Shhhh." Kim hissed. She reached up then with her thumb and forefinger grasped Bobbys rigid penis. Bobby gasped she she felt Kim's fingertips clamping gently around him just beneath the circumcised head. Gently she started corkscrewing his upper shaft beneath the mushroom head with her thumb and forefinger causing Bobby to gasp even louder. She ran the ball of her thumb over the tip at his urethral silt causing Bobby's penis to flex. Before long pre-cum started oozing out from the slit making the head nice and slippery. Grasping his upper shaft again beneath the head, Kim slid her fingertips all the way down the rigid 4" inch length to the hairless root. Holding his shaft firmly Kim leaned over, jutted out her tongue to lick the circumcised head, tasting his bubbling pre-cum. "Oh God!" Bobby gasped, having no idea that Kim would actually do that to him. His shaft flexed again. As she started to stroke Bobby's lower shaft up and down she inched in even closer to him then opened her mouth to take just about the entire length into her mouth, pursing her lips tightly around the now ultra-sensitive throbbing shaft. Instinctively both of his hands grasped the sides of Kim's head. "Ohhhh!" Bobby gasped again, this time even louder as she started to suck him off, bobbing her tightly pursed lips up and down around him. It didn't take long for Bobby to quickly reach his point of no return. "Oh, oh,ohhh." He cried out even louder as the feeling within intensified to its breaking point. A second later, he erupted like a volcano, spewing his cum like it was red hot lava into Kim's hot sucking mouth. Kim gulped then gulped again as she sucked him dry. She did not pull away until Bobby was totally spent with his penis wilting in her hot hungry mouth. "There, that will take care of that problem." Kim smiled, standing back up. She handed Bobby her bloomers. "Now put them on." She instructed. With trembling hands his cock now tingling pleasantly in post orgasmic afterglow, Bobby pulled Kim's bloomers on. "That's looking good. Now its just a matter of what type of dress I want you to put on." Kim stated. She walked over to her closet and rummaged through the dresses that were hanging up in the closet. She found a frilly yellow and pink dress then carried it over to Bobby. "This one looks nice, now go ahead and put it on." Still in post orgsasmic afterglow, with trembling hands Bobby pulled the dress that Kim had given him on. Because Bobby had never worn a dress for obvious reasons, before Kim helped him with all the little details of putting the dress on. "There!" She grinned, stepping back to admire him. "Now for the laced shoes." She found a pair of her ankle length shoes then handed them to Bobby. Because he had her dress tightly on, Bobby founded it a little hard to move, but somehow he managed to sit down. He took off the shoes that he had on then pulled on Kim's shoes. They were definitely tight and did hurt a little but after pulling, struggling and grunting he finally managed to get them on. "Now for the makeup. Come over to the bureau." Bobby stood up and painfully walked over to the mirrored dresser. Wearing Kim's shoes made it hard for him to walk. Kim had Bobby sit down in the chair, then opened up the top of her bureau to take out her makeup kit. For the next fifteen minutes Kim used eye shadow, darkened Bobby's eyelids. She used powder to make Bobby's cheeks look deeply blushed and lipstick on Bobby's moist lips. When she finally finished Bobby looked exactly like the dancehouse girl, the girl that she wanted to create to satisfy her fantasy. She stepped a little to admire her handy work. "You look perfect." She grinned. Looking at himself in the mirror behind Kim's bureau, Bobby frowned. "I look like a damn floosy." He pouted. "Oh come on Bobby, it's not that bad." Kim smiled. She leaned over and kissed Bobby a kiss on his cheek. "Can I take this girlie stuff off now? I have to get ready to go with Antonio at 4:00 this afternoon, and I don't want to look like a girl when I go with him tonight." "Go ahead Bobby." Kim said. Bobby wasted no time pulling off all the feminine clothes that he had on tossing them on Kim's bed. He grabbed his pants and quickly pulled them on. "I'm going to go on ahead and take a shower. It's going to take forever to get off all this makeup that you put on me." "Go ahead Bobby. I'll wait for you." Kim said. Bobby left Kim's room then headed to the bathroom. It didn't take long for him to get underneath the shower. As Bobby figured it did take a while for him to get all the makeup off his face. The only makeup Bobby still had on and couldn't get all the way off was the lipstick on his lips. That would have to eventually wear off Bobby concluded knowing that it would be almost impossible to rub off. He went on ahead and dressed into his clean clothes throwing his dirty clothes in the laundry hamper. He then rejoined Kim who was in the parlor playing the piano. He sat down and listened to her. She was playing a little ragtime music. "I didn't know that you played the piano." "Mom taught me. She can play the piano really good. " Kim replied. She switched over from the ragtime music that she was playing to George M. Cohen's popular song, It's A Grand Old Flag that came out during the Great War. While she was playing the piano Dot walked in. She sat down on the sofa to listen to her daughter playing the music. She started clapping to the beat. As she was doing so, Bobby joined her. When Kim finished playing Dot and Bobby clapped their hands in response. "Very good dear. Your turning into a good pianist." "I had a good teacher." Kim replied looking over at her mother. Turning to Bobby, Kim said, "A nyway, I have to go get my newspapers to sell during tonights commuter rush hour so I probably won't see you until sometimes tomorrow morning." "I'm going to have to get ready to go also. Antonio says he's going to pick me up around 4:00." "It's almost 2:00 now. If you want I can fix you both up a quick lunch." Dot suggested. "That sounds good." Kim agreed. "I am a little hungry." Bobby added. Dot left Bobby and Kim then headed into the kitchen to fix them a quick lunch. She made them a couple of tuna fish sandwiches and opened up a can of Campbells Tomato soup. After they ate lunch Kim took off to go pick up her newspapers. Bobby stayed behind and decided to take a little nap until Antonio came over to the boarding house to pick him up. Around 3:30 Antonio arrived. He talked to Dot for a few minutes then went upstairs to Bobby's bedroom to wake him up. "Time to go Roberto." Antonio softly said as he was gently shaking his shoulder. Bobby's eyes fluttered open. He sat up looking up at Antonio. "Hey." He sleepily said rubbing the sleep out of his eyes. "You're still worn out from last night, aren't you kiddo?" "I reckon." Bobby replied. He stretched then yawned. "What's that on your lips? Lipstick?" Feeling a little embarrassed Bobby said, "Yeah, Kim wanted to see what I would look like if I were a girl. She combed back my hair, had me wear one of her training bra's, knickers, and a dress, then she put makeup all over my face, it was terrible." Antonio laughed as he listened to Bobby's story. "I wish I was here to see that. I bet you looked good as a girl." "I don't even want to think about that. Anyway I tried to get this lipstick off and it just won't come off." "That's alright. It'll wear off eventually." "I hope so." Bobby stated. About a half hour later Bobby was climbing into Antonio's truck. The first thing he noticed was a pistol sitting on the dashboard. Easing into the other side of the truck, Antonio looked over at Bobby and noticed a look of concern etched across his young face. "You have a gun with you?" Bobby asked warily. "I always carry a gun with me, just in case you know. There is always the possibility that the feds getting on us. I would much prefer a shootout with the feds then going to prison." Bobby could relate to that. If the feds were to catch them, then for sure he would be sent back to Pine Island and do extra time. Pine Island was the last place that he wanted to go too. "Anyway, it is 61 miles from here to Baltimore. Once I pick up the booze from the warehouse, I'll have eighteen deliveries to make between here and Baltimore tonight so we better get going." Antonio exclaimed. He cranked up the motor, put the truck into gear then took off. A few minutes later they were out of the city of Point of the Rocks and heading down the main highway towards the warehouse to pick up the crates of liquor that would be delivered too the various honkytonks and road establishments on the road towards Baltimore. At the warehouse it took Bobby and Antonio a while to load the numerous crates onto the back of the truck that were going to be delivered that night. By the time they finished that backbreaking work the sun was slowly beginning to sink in the western horizon. When they finally finished, Antonio spread a large tarp over the crates of whiskey in the back of the pickup truck that were too be delivered. Their first stop was at a small roadhouse about fifteen miles east of the warehouse too deliver a couple of crates of whiskey. At that roadhouse they relaxed for a little while and Antonion did something that he normally wouldn't do and that was leaving the truck to enjoy a delicious steak dinner with all the trimmings. Around 9:00 that evening they were once again on the road heading for their next dropoff point. At a small honkeytonk. At this honkytonk they followed through with their regular procedure where Antonio would sit in the truck too watch while Bobby carried the crates of whiskey into the establishment then collected the money too bring back to Antonio. By now the sun had set in the western horizon and night had settled in. Things had been going well until around 12:30 that morning. They had to deliver eight crates of whiskey at an establishment called Tex's Roadhouse and Grill, a fairly large establishment and dance hall ten miles east of Baltimore. They were a little more then halfway done with the deliveries that night and were about to head back to Point of the Rocks to complete their deliveries at about four more establishments on the higthhway between Baltimore and Point of the Rocks. Under a full moon Bobby struggled with the crates of whiskey carrying one crate at a time from the pickup truck too the back of the Road House. He had finished with the last crate and had about $120.00 in his back pocket to give to Antonio when it happened. As he was heading back through the crowded parking lot towards the truck parked in the back of the parking lot two bright searchlight beams ripped through the darkness shining directly on the truck that Antonio was in, waiting patiently for Bobby to deliver the money too him. Bobby quickly ducked behind an old Model T Ford sensing that something had gone wrong. "This is the police, do not move!" He heard a shout through a megaphone. And then the first shot rang out that came from the pickup truck. Antonio was using the pistol that he had and had opened fire on them. Gun fire was exchanged, and within seconds the pickup truck was surrounded by at least twenty policemen and feds. "Come out with your hands up!" The voice from the megaphone repeated. But Antonio wouldn't yield. He started shooting at them again. Finally the police and feds who had surrounded the pickup truck opened fired on the cab of the truck at about the same time. The front window and side windows of the truck shattered, disintegrating completely into nothing. There was no way that Antonio could survive the barrage of gun fire that rained down on him. Watching all this Bobby felt sick. He had to get out of there as quickly as possible. The last thing he wanted was the police to catch him with the money in his pocket. If they caught him that would be a sure ticket back to Pine Island. He stayed hidden for another few minutes or so watching as the feds and police pulled Antonio's bullet riddled lifeless body out of the truck. Within minutes they would be searching the parking lot to see if he had an accomplice. He saw his chance then took off, keeping himself hidden low behind the numerous parked vehicles. He had to get to the other side of the road and into the woods without being seen. "We need to search the parking lot to see if anyone else was with him." He heard someone say. With drawn guns the police and feds were beginning to break up to search the parking lot. Bobby willed himself to move faster because the full moon shining brightly down on him would be against him. As bright as the moon was there was no doubt in Bobby's eyes that he could easily be seen if he wasn't careful. He stayed low and kept moving. Finally he reached the road. So far he had been lucky because they hadn't seen him yet, but he still wasn't completely out of the woods. He had to make it across the road. He took off, running across the road finally reaching the woods that was on the other side of the road. He ducked into the woods, then slid down an embankment. At the bottom of the embankment he took off running again. He fought his way through the woods having no earthly idea where he was going. All he knew was one thing and that was to get as far away from the road house, the police and feds as possible. About fifteen minutes later, Bobby finally felt safe. He stopped, sat down to catch his breath and rest for a few minutes. It wasn't until a few minutes later it dawned on him. He could never go back to the boarding house that was at least sixty miles away. He would probably never see Kim and Dot again. He was on his own. But this time though he didn't have anything else too his name he had money, at least one hundred and twenty dollars that he had collected from the proprietor for payment for the whiskey that had had purchased from Antonio. He felt sure now that the road house right now was probably being raided by the police and feds. So all in all the money he had that was in his pocket was his now. Another thing that was now in his favor was the sound of a locomotive whistle that was about a half mile away......